


Sore Winner

by ObsidianRomance



Series: Drunk!Dean 'verse [2]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Barebacking, Bottom Sam, Drinking Games, Drunk Dean, Drunk Sam, Exhibitionism, M/M, Rimming, Top Dean
Language: English
Status: Completed
Published: 2014-07-13
Updated: 2014-07-13
Packaged: 2018-02-08 16:59:31
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,494
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1949124
Author URL: https://archiveofourown.org/users/ObsidianRomance/pseuds/ObsidianRomance
Summary: <blockquote class="userstuff">
              <p>Sam and Dean are enjoying some downtime at a bar when Dean gets bored and proposes the most ridiculous drinking game ever. Porn ensues.</p>
            </blockquote>





	Sore Winner

**Author's Note:**

> **Disclaimer** : I do not own these characters.  I am just using them for fun.  
>  **Beta** : The ever lovely [](http://demondetox.livejournal.com/profile)[**demondetox**](http://demondetox.livejournal.com/).  Thank you so much for beta'ing and putting yourself at risk for sexual frustration. XOXO  
>  **Author’s Note:** After a conversation with [Kinkajou](http://kinkajou.livejournal.com/) about The Misadventures of Drunk Dean, I decided to write a drunk!Dean story everyday my job was closed due to snow. I successfully completed the challenge (List of Drunk!Dean: [Stealthily Oblivious](http://obsidianromance.livejournal.com/72266.html), [Finding Fault](http://obsidianromance.livejournal.com/70942.html),[ It's Going To Be A Long Night](http://obsidianromance.livejournal.com/72825.html), [Making Good On Promises](http://obsidianromance.livejournal.com/71510.html), [Down and Dirty](http://obsidianromance.livejournal.com/71321.html) ). I started this story when I woke up to heavy snow but I was called into work and had to abandon it. I thought I would have other snow days to work on it but I didn't. So, I finished it because I wanted to. I have one more drunk!Dean story where he very unsuccessfully does a striptease for Sam. I will post that eventually. I  hope you like it!

“I’m bored as shit waiting for something to happen in this town. We’re going to play a little game,” Dean states as he throws back the last remains of beer in his bottle.

“What now?” Raising an eyebrow, Sam gives his brother a skeptical look. He thought the man would have been plenty happy to have nothing to do after the onslaught of cases they’d been working. Hell, _Sam’s_ happy to do nothing. In fact, sitting around in a crowded bar with _nothing_ to do sounds pretty near perfection. He’s tired and he needs a break. However, he’s not surprised that Dean can’t sit still. That happens more times than he can count because Dean’s always itching to move on to bigger and better - translation: dangerous - things. Shooting his brother a knowing look, he shakes his head. “So order another beer and go play some pool.”

“That’ll be fucking boring in this place. No one would be enough of a challenge to keep me occupied. I figure drinking’s the best option we got but,” he gets a devious look on his face and licks his lips, leaving Sam to guess how he originally planned on ending the sentence.

“What?” Sam says with arms raised in expectation.

Dean just smirks and leans over the bar far enough to get the bartender’s attention. “Sweetheart?”

Sam thinks, under any other circumstances, Dean’s actions would be unwelcome and kind of condescending. But the word “sweetheart” on Dean’s lips is anything but and even Sam’s gut twists in arousal. It’s a weird reaction, considering Sam would kick Dean’s ass six ways from Sunday if Dean ever turned the expression on him. Still, the smooth, deep quality of Dean’s voice makes a lot of words sound good. Sometimes, Sam blames Dean’s voice for the fact that his older brother is able to talk him into doing anything.

For now, Sam’s content to roll his eyes at Dean’s attempts to flirt with the bartender and occupies himself with noticing the way Dean’s ass curves in his jeans when he bends over the bar top just right.

Dean catches Sam looking and smacks him on the back of the head. “I was going to give you one of these beers I just ordered, but seems to me your mind is other places than drinking in a bar.”

“Shut up, jerk.” Sam snatches the beer before Dean can pull it away. Whatever Dean’s doing, playing coy or whatnot, it’s a ridiculous pretense. They’ve been sleeping together for years, been exclusive for half that time. Besides, it’s not like Dean doesn’t check out Sam’s _everything_ on a daily basis.

“Bitch,” Dean mumbles before busying his mouth with taking a swig from his beer. “So, like I said, I’m bored. You up for a challenge?”

“What kind of challenge are we talking about here?”

“One where I win.” Dean pauses in wait. He knows as well as Sam does that Sam won’t be able to ignore the still unanswered question dangling in front of him. He’ll take the bait like he always does. His fingers thumping along the bar, it’s almost as if Dean is keeping track of the seconds between the time he stopped talking and Sam finally gets nosy enough to butt in. At the first sound of Sam’s voice, he smirks triumphantly.

“And what are you winning, exactly?” Sam immediately takes a gulp of beer because he feels like he’s going to need it to help pave the way for whatever Dean’s so damn giddy about.

“It’s simple, really. There are tons of people filtering in and out of this place. I am proposing that every time one of them, male or female, checks either of us out, the other person has to drink. Last one standing wins.”

“That makes no sense. How does anyone _win_?” Sam snorts.

“Well, I get eye-fucked by most of the people here and you get too shitfaced to remember your name. Proves I’m the better looking one and comes with the added bonus of having blackmail material over your drunk ass for weeks.”

“Fuck that!” Sam elbows Dean in the ribs. “That is _not_ how it is gonna go down.”

“Oh, yeah? Prove it.”

“Fine. I will.” Sam sets his stance and stands at full height. Stepping back, he realizes there are quite a few people around them. He’d tuned them out, letting them all filter into the background as he got lost in spending downtime solely with Dean. A pretty blonde on the outskirts of her group makes eye contact with Sam, followed by a definitive full body scan and smirk of approval. Her eyes get snagged around crotch level and Sam thinks the gesture is about enough that he has to see. Turning to face Dean head on, the word, “drink” drops from his mouth in a monotonal command.

Dean rears back and screws his eyebrows in confusion. “What?”

“I said, ‘drink’. That girl over there wants my junk.” He nods his head in the blonde’s direction and smiles proudly.

Dean sidesteps Sam and gets a better look at the girl. Now that she knows he’s watching, she pretends to stare at the ceiling while combing her hair with her fingers. It’s too late, however, because Dean’s already saw enough evidence that Sam was telling the truth. “Well, shit.” Shaking his head, he takes a swig of beer. “A deal’s a deal.” He settles himself on a barstool and scans the area.

Sam watches what happens next. It’s not much of a stretch. Dean’s a good looking man and Sam’s gotten used to him getting the once over _more than once_. His change in positioning around the bar catches the bartender’s attention and she gives him the slightest jerk of her head and what Sam assumes is her version of a sexy bite of her lip.

“Drink,” Dean says triumphantly as he pushes Sam’s beer towards him. “She’s done that several times tonight but I didn’t think it counted unless you saw it.”

Sam rolls his eyes and drinks.

The next hour is spent with a steady flow of people noticing them. It’s kind of hard not to. They’re _big_ in a lot of ways, height only being one of them. There’s a guy who is with a girl but ends up staring a hole in Sam’s clothing.

Dean drinks with a snort.

There is a girl who outright stares at Dean, leaving Sam to drink but Dean to deal with the girl’s jealous boyfriend who is trying to pick a fight with Dean.

“Listen man, I’m not interested.” Dean seems to look through the guy like he doesn’t really give a shit. And maybe it’s because he’s got a steady buzz going, he slips his hand down Sam’s back and squeezes one of the round globes there. “Got other things on my dance card.”

Sam’s eyes go wide as he almost spits his beer out from his nose. He hadn’t been expecting any blatant shows of affection, much less being thrown into a sort of pissing match between two men trying to assert their claim.

The tactic, however, works. The guy’s jealousy fans out and he retreats with a scowl on his face. But people noticed Dean grabbing Sam’s ass and they are _interested_. It earns Sam and his ass another two members in his fanclub and he finds himself buying Dean another beer so he can take two big swigs.

Things get more interesting after that. They turn around so their backs are leaning against the bar and their eyes search out anyone who looks interested. They finish another two beers each and Sam’s not exactly sure who is winning but they’re both still standing tall.

“Time for something a little stronger.” Dean’s words are slightly slurred but his movements are precise when he spins around and leans over the bar. The bartender’s still crushing on Dean and is quick to serve him the two Johnnie Walker on the rocks he ordered, a little heavy handed on her pour.

“Dean. No.” Sam says with a shake of his head but he knows he’s going to be drinking the whiskey away. He’s triplely doomed when a trio ofgirls walk into the bar and _all_ give Dean a thorough inspection. There are giggles, whispers, and more lusty thoughts. They are _definitely_ thinking of his brother’s dick. “Crap.”

“Just drink the whole damn thing.” He’s laughing as Sam brings the glass to his lips. Reaching out, Dean tilts the bottom and forces the golden liquid into Sam’s mouth. Sam sputters before he gets his throat to cooperate and swallow. When he does, Dean thumps him on the back. “That’a boy.”

Sam glares at his brother, more determined than ever to get Dean so shitfaced he won’t be able to see straight. The problem is, Sam’s beginning to see double. Well, not _double_ , but there is a blurred quality to everyone. Trying to one up Dean, he makes eye contact with a man across the room, skims one of his big palms down his chest and lets it come to rest over the zipper of his fly. He squeezes suggestively and the man’s smile twitches into a smirk. Sam watches him elbow his buddy and they both give Sam a look. “Drink up, Dean,” Sam says as he cuts off the line of attention with the two men. “I bet I can find a third person too…” his words trail off as he twists his head and picks up on a girl who had been staring at his ass. “There!” He points towards her and the girl flushes, turning away so quickly she probably has whiplash. “Down it.”

Dean doesn’t hesitate. He kicks back the liquid and slams the glass on the bar, making sure to call loudly for another round.

The night, and their blood alcohol level, gets a bit more intense. Sam and Dean are standing so close together that they share the same air and shoot off waves of heat. Two women approach them but don’t do much. Sam takes a gamble and yanks Dean by the collar of his shirt. Their lips meet in an unsteady kiss but it only takes a moment for both of them to get on the same page. They kiss the way they always do: intense and with the type of roughness that always comes with deep-seated want and dedication. Only breaking apart when the need for air takes over, they take deep breaths in tandem. For a moment, their eyes are locked on each other and clouded with lust but their brotherly competitive spirit runs deep and they turn to see what effect their kiss had on the two women.

The women seem frozen in their spot but their lips are parted as if they’d let out a shocked gasp that Sam and Dean were too preoccupied to hear. Their eyes are filled with want and Sam thinks he sees the one on the left twitching her fingers as if already thinking about what they could do if they were on either of the men.

They give a clear appreciative sigh and continue to check Sam and Dean out.

Shrugging, Sam and Dean make eye contact. “Guess we both drink on that one,” Sam says.

Dean can’t leave well enough alone. “If you had to pick one of us,” he asks the women and they almost startle at the sound of his voice. “Which one would it be?”

The women blink for a moment but the one on the right finds her voice and squeaks out. “B-both?” She licks her lips and bites her knuckle.

“Well, shit.” Dean grumbles. He turns towards Sam, forgetting the women, and lifts his glass. “That one is a tie.”

They share a drink and get more determined to see this competition through.

They play dirtier. Dean grabs a cherry from the bar and sucks the thing the way he sucked Sam’s asshole last night. His tongue rolls around the red fruit before he plucks it off the stem and licks his lips. It earns him quite a few looks and another drink from Sam.

Sam can play dirty too. He can unbutton his shirt because _it’s fucking hot in the bar_ , and he can shimmy his jeans down enough to expose the V of his hips. He can do all those things and get Dean another drink because the man’s going to need it after how many people have their jaws on the floor.

The problem is, they get _too_ drunk. They drink _too_ much and forget the rules. They drink twice if someone has the nerve to ask them to have a drink with them. They inform the hopeful Casanovas that they have a drink and a person to drink with, so they are good. But they appreciate the flirtations. Soon enough, they are taking a drink from their own glass when someone tries to flirt or hit on them.

The mental scoreboard they’ve been keeping gets muddled.

It’s over when Sam and Dean are facing each other and Dean takes a drink without any foreseeable reason.

“Wha?” Sam says. He sounds a little sleepy but it’s because he’s on a happy, fluffy, alcohol induced cloud and he’s looking at the hottest man he’s ever seen. Dean looks _good_ and Sam’s mouth is practically watering.

“My turn to drink since you’re starin’ at me. Pro’ly havin’ lots of dirty thoughts up in that brain of yours. You fuckin’ me Sam or am I givin’ it to you?” He swallows thickly in indication that he’s probably having the same thoughts.

He’s actually imagining both scenarios happening in sequence. It hits Sam then that he’s completely trashed and tries to get to his feet to kiss the dirty words off Dean’s lips. He stumbles and the only thing that saves him from cracking his head open on the floor is Dean’s arms closing around him. He has a lot of snarky comments to throw his brother but all he gets out is, “I want your dick.”

“I can give you that, Sammy.” Dean smirks, eyes glazed with intoxication. “You gotta admit I win. Admit it and you can have my dick all you want.”

“You win,” Sam breathes out against Dean’s neck despite the fact that he really doesn’t want to give Dean the satisfaction of being the winner. The thing is, he wants Dean’s dick more. “You win. Fuck Dean, kiss me.”

Dean does. He grabs Sam’s jaw with both hands and kisses him, making sure his tongue fucks inside to toy with Sam’s.

Sam floats in the moment. His brain is fuzzy but he’s thinking clearly about how much he loves Dean and the way their lips work together. It leaves his whole body vibrating with the intensity of their connection.

“Come on,” Dean says when he breaks the kiss. He pulls Sam by the arm, making his younger brother stumble until he’s far enough from the bar that Dean can get an arm around him. “I always did handle my liquor better than you.”

“Fuck you.” Sam slurs with a goofy grin and his arms clutching Dean.

“Not tonight. Tonight you’re too shitfaced to piss straight, let alone fuck me enough to get me off. I want your very drunk ass. Been sick of people staring at it all night.” He growls possessively as he maneuvers them out of the bar.

It’s a good thing their hotel is a very interesting 5 minute walk down the road. Sam sidesteps more than he actually moves forward and if it wasn’t for Dean pushing him forward, they would have ended up in the playground on their right.

Dean shoves them into the hotel room, leaving Sam to fall onto his knees. He scrambles to get up, using the foot of the bed to pull himself up and he crawls like a baby to drag himself in the middle.

“Shit, Sam. You think you can get your pants off or need a hand,” Dean reaches out and works to open Sam’s jeans.

“I got it!” Sam slaps Dean away with a raised lip. He’s drunk but he _can_ get his jeans off. He _wants_ Dean and it’s all he can think about. His pants come off with a bit of a struggle and soon enough, Dean is nude as well and blanketing Sam so that their dicks slide together.

“Dean,” Sam breathes out and stretches his whole body. He feels every fiber of his being and the way they are buzzing and adrenaline rushes through him. Bucking up into Dean’s arousal, he moans. Their lips are busy working against the other’s and he reaches down to curl a hand around both of their dicks. “That’s mine. I didn’t like people thinking about what it would be like if they could touch you like this.”

“Yeah. Yeah. Yours, Sammy. They’d never get it.” Dean kisses Sam’s jaw and over his pulse point. “Though, those two women who looked like they were ready to have a foursome with us might have been interesting.”

Sam growls. “Mine,” and he tightens his grip, making Dean yelp for a second. Seemingly getting his point across, he twists so he can get his lips on Dean’s mouth. Kissing him now reminds him how the bar has followed them home. Dean still tastes like the sweet aftershocks of whiskey and beer and Sam tries to licks all traces out of him. A moan escapes his mouth and it’s so dirty and far gone that Sam blushes. He can’t believe what Dean has whittled him down to. He’s a needy mess.

Dean seems to like it. Licking his lips, he flips Sam onto his hands and knees and yanks his ass in the air. Even drunk, they know each other’s bodies inside and out and it’s not hard for Dean to make Sam open up and fall apart. “Love your ass,” he moans as he puts a hand on each ass cheek and spreads Sam open to reveal the tight ring of muscle. “You thought the cherry got it good tonight? You’re gonna get it better.”

Getting to work, Dean’s hands squeeze the muscles of Sam’s ass. His tongue is relentless and doesn’t waste time in pressing up against Sam’s entrance. It teases, pushes, and stretches, making sure to lick Sam gently when he needs to come back down from his careening. He hesitates for a moment to make sure Sam can handle it and then goes all out, eating Sam out so thoroughly that his little brother loses his composure and falls flat on his belly. He’s shaking uncontrollably and arching back into Dean to get the widest part of his tongue inside.

“Shit, Dean! More.” Sam tries to get on all fours again to give Dean better access but he just doesn’t have the coordination.

Dean does it for him. He yanks Sam up and holds him there. There are more important conquests on his list and he isn’t letting Sam sit this one out. Sucking on two fingers, he starts to work one, then two, in beside his tongue. It’s hurried but not in the sense that Dean’s neglecting making sure Sam’s prepared enough.

Sam chokes on a moan and feels the way Dean’s working the most intimate parts of him. Sam’s entrance sucks Dean in, fluttering and relaxing enough to make sure those fingers get deep enough to curl and brush Sam’s prostate.

“Come on, Dean. What ‘cha waiting for? Fuck me like all those other people wanted to. Remind me that they can’t have what we have. Not like this.” He moans and knows his cock is leaking against the bed, drops of pre-come leaving sticky traces on his belly. “Fuck me. I’m good. I want it. Been thinking about your dick all night. Those people...they’ll never know. But I do.” Sam’s voice sounds a little desperate, like he’s strung out and the alcohol is exposing them. They’re naked and riled but there is also this raw quality to everything. It’s more than just a possessive trait. They love each other in a way Sam’s sure _no one_ can ever comprehend. That’s what it is.

They’re buzzed and in love and riding that rush.

Sam spins, forcing his brothers fingers and tongue to slip away. He gets them face to face and kisses Dean’s spit slick lips. “I fucking love you.” He wanted it to sound less lame and as intense as the emotions coursing through his heart. He _wanted_ it to sound less cliché and more _them_ but it’s all he’s got.

Dean smiles as bright as a light bulb and says, “gonna fuck you, Sam. Want it?” The words have a literal meaning, but it’s almost like they are a perfect response to Sam’s declaration. Dean reaches down and fumbles with his bag, pulling out a bottle of lube and making quick work of slicking up his own weeping arousal. 

“You know I want it. Always do.”

“Yeah, you do, don’t you?” Dean bites his lip and takes in the sight before him. He leans in and brushes his lip against Sam’s ear. “Me too.”

As drunk as Sam is, he manages to spread his legs for Dean, exposing his prepped entrance. Dean gets stuck staring at that for a moment but Sam puts each of his long legs over Dean’s shoulders. “Come on, Dean. Push my legs back. Fuck me like this. You won tonight. My ass enough of a prize?”

Dean seems lost in his own thoughts, pupils blown wide with want, lust, and intoxication. With one hand on Sam’s hip, he guides the tip of his cock past the ring of muscle. Like always, they both let out a satisfied moan that lasts for the duration of Dean’s initial thrust. Dean stares the whole time, watching his dick split Sam open until he is fully seated and Sam can’t stop making pleading noises.

“Dean, you better fuck me or I - ” The wind is punched out of Sam and he never gets to finish his threat because Dean shoves forward and starts fucking him.

The pace they set is brutal and builds thrust after thrust after _thrust_.

Each push of Dean’s hips is met with a slap of skin and moans.

They are _not_ quiet. There is an angry slap against the wall from the adjoining room and Sam moans louder. They are breathing heavily and their shouting is probably carrying all the way to the lobby.

“Come on, Dean! Harder! Fuck me harder!” Sam’s lost to it. He tries to get up on his elbows to watch the activity between his legs and almost comes at the sight of Dean’s glistening dick pummeling him. Arching, he gets Dean to hit his prostate and sees stars. “Oh fuck, yeah! Just like that! God you’re so good.”

“I know” Dean smirks and looks Sam in the eyes before leaning back enough to _really_ see how his dick is getting sucked into Sam’s tight heat. His hips keep rocking off the bed, but leaning back, he is able to hold Sam’s legs open a bit wider and a moan rumbles through him. “Look at you. You take me so good.” The angle changes everything. Dean’s buried deep and keeps plowing into Sam’s tight ass, his muscles straining as he keeps himself fully sheathed before pulling out and repeating the process. They’re both drunk but Dean’s still able to manage this feat of orgasmic achievement. It’s impressive that he’s able to keep it up for so long, but his hips keep moving and Sam keeps moaning. They’re covered in sweat and by the time he gets his hand on Sam’s dick, they are too far gone. There is a wet pulse of come that serves as the beginning of the end of them.

”Gonna come, Dean.” Sam’s voice is wrecked, shaking just like every muscle in his body.

“Good,” Dean pants out. The hand he has around Sam’s dick gets a better grip and he moves it in time with their hips, thumb sweeping up over the head.

Sam manages to push himself upward. It’s impressive since his legs are still over Dean’s shoulders but the move gets Dean deeper and it’s almost too much for Sam. It sends his head spinning. Reaching out, he gets his arms around Dean’s neck and kisses the man silly. His brother is so deep inside of him that he can taste it and he loses it. Ropes of come shoot from his dick between them and he _needs_ air but he doesn’t break the kiss with Dean. He thinks, maybe, he needs Dean more than air at this very moment.

After several more frantic trusts, Dean comes. It’s evident by the way he groans through his orgasm and Sam can feel wet splashes of Dean’s release slicking him up from the inside.

They’re both fucked stupid but Dean manages not to collapse on top of Sam. They land in a come splattered, sweaty mess of limbs beside each other. They’re gasping and smiling at the same time, and Dean looks thoroughly proud of himself.

“I fucking win,” Dean says.

Sam isn’t sure why it still matters but then his brain has enough juice to remember that it’s _Dean_. He thinks, however, that they both won something because he feels _good_. He’s fucked in all the right ways and warmth from the whiskey works its way through his system. He’s going to be stuck with one hell of a hangover tomorrow, but that’s tomorrow. Right now, he wants sleep. Lots and lots of sleep where he doesn’t dream about monsters and death, but Dean’s amazing dick instead.

“Yeah, you win. Happy?” Sam snorts.

“Fucking thrilled,” Dean says and he’s definitely slurring everything right now. Whatever part of him that was still sober left along with his come. “Gonna go clean up,” he mumbles as he tries to get to his feet.

Only, Dean doesn’t stay upright. He stumbles and falls, landing on the floor beside the bed. Groaning and whining, he reaches a hand up and searches for contact with Sam. “Sam? Sammy? _Sammy?_ ” His calls get more demanding and pathetic as they go on. “I can’t use my legs right now.”

Snorting, Sam shakes his head. He loves him but his sore winner of a brother can stay on the floor.

“SAMMY!” Dean yells but it’s so slurred that Sam only knows what he’s saying because he’s heard his name on Dean’s drunk lips too many times before.

Rolling over, Sam pulls up a sheet. If Dean’s still on the floor when he wakes up to pee, _maybe_ he will help him out. Right now he figures that lying on the floor isn’t going to do Dean any harm. Besides, he’s pretty sure he can still use his legs right now: it means he wins.


End file.
